Coupling reaction is an important reaction in the generation of carbon-carbon bond and carbon-heteroatom bond. Compounds produced by coupling-reaction, such as aromatic amine compounds, are useful as hole-transport materials and luminescent materials used in organic electroluminescence elements, etc., and numerous structures are proposed for these compounds. In addition, aromatic compounds manufactured by utilizing the Suzuki-Miyaura reaction are used as intermediates in numerous drugs, agrochemicals and pigments.
One old method of manufacturing aromatic amine compound is to cause an aromatic compound containing halogen atoms to undergo cross-coupling reaction with a primary amine or secondary amine in the presence of a palladium complex and triaryl phosphine (refer to Patent Literature 1). However, these combinations produce low reactivity and the yield of the target aromatic amine compound is not sufficient, and therefore numerous studies have been conducted, and di-t-butyl (4-dimethyl aminophenyl) phosphine and other catalysts, which have abundant electrons and are sterically bulky, have been proposed as a result (refer to Patent Literature 2). There are also reports on Suzuki-Miyaura reactions using various phosphine ligands (refer to Non-patent Literatures 1 and 2).